Steakhouses in Jackson Park

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Jackson Grill: A User's Guide

Acclaimed Supper Club | Steaks and Seafood | Massive Portions | Brandy Old-Fashioned Cocktails | Retro Vibe

Sample Menu

  • Appetizer: hand-cut duck-fat fries served with housemade aioli
  • Entree: 24-ounce Black Angus bone-in rib eye with gorgonzola butter
  • Side: garlic mashed potatoes
  • Cocktail: brandy old-fashioned sour

    The Vibe: If one phrase best sums up Jackson Grill, it's "old fashioned." This descriptor applies equally to the decor of candlelit white linens and to the way the same family has run the establishment for decades. It's also the name of one of Wisconsin's most beloved cocktails, which the restaurant's bartenders strive to perfect.



    Inside Tips

    • All of Jackson Grill's dinners come with housemade soup. If you get the opportunity, select the crab bisque, which has received praise from both Third Coast Daily and the Milwaukee Journal Sentinel.
    • Arrive hungry. In addition to soup, each dinner also comes with salad, a breadbasket, and a complimentary bowl of olives. The entrees are also so big that you "might have to call in reinforcements for desserts," according to the Milwaukee Journal Sentinel.

      While You're Waiting

      • Check out the collection of framed signatures from local celebrities and venerated Wisconsin athletes in the foyer. A few of these famous folks are regulars, so try not to kiss the autographs in case they see you.
      • Try to spot Chef Jackson. He's been known to make the rounds in the dining room, chatting with guests and asking how their nights are going.

3736 W Mitchell St
Milwaukee,
WI
US

Hard as it is to hold off on the pizzas at Tarantino, it might be worth it if it means a chance to try the appetizers. Diners can begin by splitting orders of mozzarella sticks, buffalo wings, or eggplant strips. Then it's time to dig into one of the specialty pies, such as the Mexican pizza: mozzarella and cheddar cheese topped with ground beef, black olives, and onion. Pastas include lasagna, mostaccioli, and ravioli, the latter of which comes stuffed with meat, spinach, or cheese, and never a note that says, "IOU one ravioli stuffing."

2577 S 68th St
Milwaukee,
WI
US

SteakHouse 100 satisfies carnivorous cravings with a menu heavy on red meat and sophistication. Start by snacking on nature's easiest prey: escargot in mushrooms and garlic butter ($6.95 for six). Steaks—such as the 25-ounce cowboy steak ($29.95) and the 12-ounce senior New York strip ($23.95)—are cut by hand, not by laser. A quartet of surf 'n' turf options pits land against sea in a culinary cage match, and an array of sandwiches (such as Philly cheesesteak for $10.95 and marinated chicken breast for $7.95) provides meaty delight without the encumbrance of silverware. Because rib, like ministers and meridians, is better when it's prime, SteakHouse 100 also offers a trio of prime-rib options, starting with the 12- to 14-ounce junior prime rib ($19.95) and scaling up to the 16- to 18-ounce king prime rib ($23.95). A large wine list and full bar keep beef-weary jaws well-oiled.

7246 W Greenfield Ave
Milwaukee,
WI
US

Brewski's Sports Club can only be described as an adult playground. Giant screens broadcast popular sporting events, including football and baseball games. Black lights dangle over long tables set up for drinking games. A hoops game helps patrons work on their jump shot. On Sundays, bartenders mix up liquid breakfasts, including the Eggs and Bakey, a bloody mary mix paired with house-infused bacon vodka, topped with a hard-boiled egg, and loaded with cheese whips and bacon.

6024 W Bluemound Rd
Milwaukee,
WI
US

5 O'Clock Steakhouse: A User’s Guide

Award-Winning Steak House | Classic Surf 'n' Turf | Live Entertainment | Californian Wines | Supper-Club Decor

Sample Menu

  • Appetizer: shrimp cocktail
  • Entree: bacon-wrapped fillet with blue cheese
  • Drink: Rodney Strong merlot from Sonoma

When to Go: Try to plan your dinner for a Friday night around 8 p.m. That’s when musicians hit the adjoining Alley Cat Lounge stage, playing everything from oldies and jazz to modern rock and R&B.



Inside Tip: Show up hungry. All meals come with a salad, relish tray, and sourdough bread with butter and honey. A side of butter-sauteéd mushrooms also accompanies every steak.



Media Mentions: Over the years, 5 O’Clock has drawn national attention. The Travel Channel featured it on the program Steak Paradise, Saveur magazine named it one of the best steak houses in the country, and Travel + Leisure said it has a "Mad Men vibe."



Behind the Name: According to the restaurant's lore, the steak house got its name from an alarm clock that would ring every day at 5 p.m., alerting customers that it was time for a free drink.



While You’re in the Neighborhood
Before: Tour the Tripoli Shrine Center (3000 W. Wisconsin Avenue), a replica of the Taj Mahal and a member of the National Register of Historic Places.

After: If the entertainment at the Alley Cat Lounge isn't to your taste, head over to The Coffee House (631 N. 19th Street), which offers acoustic music and poetry performances.

2416 W State St
Milwaukee,
WI
US

Mr. WEBO's sets itself apart from run-of-the-mill taquerias with their full service outdoor patio and their colorful, urban murals depicting everything from diamond-studded roses to a skeleton mariachi band. The graffiti-chic decor is counter-balanced by a refined menu of updated Mexican classics made fresh-to-order with many local ingredients. Standard baja fish tacos, for example, are re-imagined with a tangy breading made from yellow and blue cornmeal, then topped with shredded purple cabbage, chipotle aoli, and avocado crema. Meanwhile, chiles rellenos arrive dredged in a corona batter and stuffed with green and red chorizo, and flourless gluten free chocolate cake awaits to provide a sweet ending to spicy meals or post-dinner food fights. One taqueria tradition Mr. WEBO's has loyally adhered to? Margaritas––which are served by the whole- or half-pitcher in a choice of six flavors.

**Groupon Celebrates Pride Month** Over the last 50 years, the gay-rights movement in America has overcome tremendous obstacles to become a powerful voice for inclusion and diversity. Even as it has grown, the movement—like Groupon—is local at heart, and we applaud the commitment to real change that improves everyday lives. At Groupon, we are happy to add our voices to those celebrating PRIDE, their achievements as a social movement and a continued march to equality for the LGBT community. Plus, we love a chance to dig that rainbow wig out of storage. This month—and throughout the year—we salute our merchants and customers who support PRIDE and all efforts that promote dignity, respect, and equal opportunity. We're highlighting these merchants' deals with a special badge to show Groupon's pride in working with people who share our values.

2301 South Howell Ave.
Milwaukee,
WI
US